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Italy Tours & Vacations in September

Embrace the plentiful charms of Italy as you explore legendary cities, tranquil countrysides, and indulge in tantalizing cuisine. September is one of the best times to visit Italy because of pleasant weather, smaller crowds, and local experiences. When you design your September tour with Zicasso your trip will be created alongside the best Italian experts.

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Let these itineraries inspire your personalized travel experience

Cathedral of Palermo in Italy

14 Day Trip IdeaFrom $5,100

Two-Week Highlights of Southern Italy Tour

Naples, Pompeii, Sorrento, Amalfi, Positano +3 more
Discover the endless charm of the Tuscan countryside near Florence in Italy

8 Day Trip IdeaFrom $7,800

Enticing Flavors of Italy Tour: Private Cooking Courses, Wine & Olive Oil Tasting

Rome, Trevi, Tuscany, Florence, Umbria
City view and Arco della Pace at Piazza Sempione, Milan, Italy

8 Day Trip IdeaFrom $3,600

The Great Escape to Tuscany Tour

Florence, Lucca, Apuan Alps. Greve, Mutigliano, Bagni di Pisa +1 more
Skyline of Florence, Italy

15 Day Trip IdeaFrom $6,800

Best of Italy and Sicily Tour

Rome, Pisa, Florence, Venice, Assisi +6 more
The Faraglioni rock formations of Capri, Italy

8 Day Trip IdeaFrom $2,900

Romantic Escape to Italy: Amalfi Coast, Rome, and Venice Tour

Ravello, Rome, Vatican City, Venice, Amalfi Coast
Manarola on the cliffs of the Cinque Terre in Italy

15 Day Trip IdeaFrom $14,200

Private Northern Italy Vacation Package

Milan, Verenna, Bellagio, Verona, the Dolomites +7 more

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  1. 1.Share Your Travel Dreams

    Zicasso specializes in custom tours, vacations, and safaris tailored to your interests and preferences. From private African safaris to culinary experiences in Europe, submit a trip request to share your ideas and travel style.

  2. 2.Meet Your Travel Specialists

    To ensure a personalized experience, we'll carefully handpick and introduce you to two of our top travel specialists, each with unsurpassed destination knowledge and local insight aligned to your luxury travel dreams.

  3. 3.Design Your Perfect Journey

    Compare the expertise of two specialists with itineraries crafted exclusively for you. You can refine these further and choose your preferred proposal. Our unique process ensures a more creative, personalized, and expertly crafted trip.

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4.9

Reviews of Zicasso's Italy Tours & Vacations in September

Based on 2519 verified traveler reviews.

Luxury Anniversary Vacation Review: Italy, Florence, Venice, Amalfi Coast, Cinque Terre, Tuscany, Verona, Naples, Vatican, Pompeii

I have to begin by saying I've told everyone how pleased I am with Zicasso and the travel agent they recommended.  I also have to say that I was very hesitant to book my trip with a company that I had only communicated with via email.  Turns out I had nothing to worry about.

The initial response I received from my agent was immediate and continued right up until our actual trip while we were in Italy.  I let her know where I wanted to go, what I wanted to see, told her I was interested in a mix of arranged tours and time on our own.  She listened and also made great suggestions.  I honestly can't say enough about how wonderful she was to work with, along with her co-worker.

They arranged for all our hotels, transportation and tours.  Every driver and guide we had was top notch.  They made a point of keeping us in small groups, sometimes only the two of us and the guide.

Our 19 day trip began in Venice where we were met at the airport and driven to a private water taxi.  That driver walked us out of the boat and made sure we knew how to find our hotel. Our departure was just as seamless.  A guide met us in our lobby, walked with us to the water taxi, came into the train station with us and explained the board to us, pointing out our train and track number.  

We continued on to Verona, Cinque Terre, Tuscany, Florence, Naples, the Amalfi Coast and Rome.  Since we weren't in any one place longer than three days it was extremely helpful to have guides, even for just a couple of hours to orient us, which saved us a lot of time.  We had guides for a walking tour in Venice, a morning in Cinque Terre traveling with us between the villages, the Accademia in Florence, Pompeii, an Amalfi Coast drive and the Vatican in Rome.  Every one of the them was passionate and proud and we learned so much.  We had a car in Tuscany and saw many other places on our own, Lucca, Pisa, San Gimignano, Siena, Montalcino, Montepulciano.  We stayed in Sorrento, spent one day on Capri and another full day on a tour to Positano, Amalfi and Ravello, which included a short boat ride along the coast.  Spectacular.  Our only tour in Rome was the Vatican but we saw all the other major sites on our own, taking the metro, bus, taxis and walking, lots of walking.  It was the perfect mix of free time and arranged tours.

And, they also worked with our children who surprised us with a dinner in Venice for our anniversary after a gondola ride!

One great advantage to having your tour guide in the country you're visiting, you're in the same time zone.  We had one mishap with a train and were able to talk to them right away.  Other than that, everything worked liked clockwork.

I would definitely use them again and have told everyone I know what a wonderful job they did for us.

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Review: Italy Family Vacation, Rome, Tuscany, Florence, Amalfi Coast, Sorrento, Positano, Pompeii, Pisa, Vatican Papal Mass

Our family of five just got back from the most wonderful vacation in Tuscany and Rome.  Our agent crafted a set of amazing experiences for our family from the private tour guides to Florence, Pisa and Lucca; a private wine tasting lunch at the Capannelle Winery and vineyards in Chianti; tickets to the Papal mass at the Vatican; to a tour beneath the church of San Clemente to see the excavations of a byzantine and then a Roman street neighborhood; a day excursion to the Amalfi coast to visit Positano, Sorrento and Pompeii; and more! Our agent and the guides found excellent restaurants from a simple salumeria where the locals ate to some high end restaurants.  The hotels were right in the center of Florence – on the piazza della Repubblica - and Rome – between the Piazza del Popolo and the Spanish Steps.  Our agent was attentive to our plans and made excellent suggestions.  Everything went extremely smoothly.  All the guides drivers were very friendly, spoke English and were very knowledgeable about art, history and the local culture.  We saw so much every day because everything was so well planned.  Simply the best travel experience ever!

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Travel Review: Family Trip to Italy, Verona, Rome, Venice, Naples, Positano, Bologna, Florence, Assisi, Siena, Pisa, Gelato-Making

My family of 6  (Michigan, USA) made a once in a lifetime trip to Italy in June 2018.

We worked with this travel agent as recommended by Zicasso, for 9 months starting in August 2017 in order to customize a trip for us to privately see the all the places we wished to see in June 2018. Our travel agent was very responsive and accommodating in working within a budget and the planning process. He provided alternatives to choose from when suggesting accommodation’s and activities. We ended up with 2 fabulous weeks touring the entire country, stopping for private tours (yes…just the 6 of us) in the following cities.

Pompeii - Amalfi Coast - Island of Capri - Naples - Rome - Assisi - Cascia - Florence - Siena - Pisa - Bologna - Verona - Venice

We were greeted at the airports and personally escorted throughout the arrival and departure process which was invaluable when you do not speak/read or comprehend Italian. Our agent set up private transportation with English speaking drivers, within and in between each city, for our family which made our experience with the local culture and communities that much more rich. The travel guides in each city were very well selected and highly educated. They took their time giving us fun facts as well as historical information about their city and its traditions. They were also accommodating with all of our requests for bathroom or food breaks, recommendations to local restaurants and additional activities. Our overnight hotel accommodations were extremely luxurious and we felt very lucky to be treated so special. Each hotel offered complimentary breakfast so we were able to start each day with excitement and full stomachs.

We would highly recommend this travel agent to schedule anyone’s tour in the beautiful county of Italy.

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Review: Italy Tour of Pompei, Capri, Paestum, Florence, Chianti
The trip that was designed for our family of 4 trip to Italy had the perfect balance of all our interests. It was amazing, and the travel team kept in touch with us at every step, from planning to texting us contact information and arrival times for tour guides and transportation. Great combination of authentic old town Salerno including a fabulous view from the B&B rooftop terrace, and fresh baked breakfast at the cafe. Salerno location was convenient for all our tours to Pompeii and Paestum. The ferry boat ride to Capri was a bit long, but offered fantastic waterfront views of several Amalfi coast towns along the way. Blue grotto was worth the wait. All of our tour gudes were all amazing, very knowledgeable and animated and kept the kids interested. The short Florence walking tour was perfect to get to know the historical churches and piazza sites, while not overwhelming the kids with too much art history or museum stuff. The tuscany bike tour was a fantastic and interactive way to see the country. The travel company organized the days and times perfectly and we were able to enjoy free time every evening. There was so much variety and a great mix of family activities and history.

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Italy Family Vacation Review: Rome, Florence, Venice, Sorrento, Positano, Amalfi Coast, Naples, Mt Vesuvius, Glass Blowing Class

WOW!  Where do we start.  It was a fantastic family vacation.  From start to finish, we couldn't ask for a better scripted trip.  Our travel agent, was responsible for our itinerary for the entire trip; boy were we glad we've used their services.  They were pure angels holding our hands the entire trip.  Our travel agency would check and remind us of our itineraries on a daily basis.  It really felt as if they were right next to us.  Thank you to our agency!

We started out in Venice for 3 nights, travel to Florence for 3 more, then to Sorrento  via Pompeii 3 there as well, then to Rome for final 3 nights.  

Once, we arrived in Venice, our contact met us at the airport to guide us to our hotel.  I highly recommend it since it's not an easy place to navigate on your own the first day.  After checking in, we met our tour guide for our first guided tour.  It was a walking tour of city of canals.  Just beautiful!  Next morning, we met our guide again but for Burano & Murano.  We loved the different pace of these islands.  After completing our tour we met our instructor at his glass blowing studio for a hands on experience, just lovely, follow by a Gondolier Class and Food Tour.  It was perfect way to finish the day.  On the third day, we took a one hour train ride to Verona, birth place of Romeo and Juliet.  Our tour guide met us and showed us around town and its history.  It was an wonderful place to visit.  Upon returning from Verona, we had the evening to ourselves.  We started out walking around to explore.  Needless to say we got lost but that was for the best.  It gave us the opportunity to explore the city and see how the locals lived.  

Florence was our second stop.  We met our guide for the tour of the city including Santa Croce church.  Following day we visited the Accademia Gallery & Uffizzi Museum which is a must when in Florence.  On the third day, we had a lovely day trip to Pisa.  Little bit of a bus ride but wouldn't have missed it for the world.

Sorrento was next on the agenda.  But first, we stopped at Pompeii.  Our guide, an archaeologist, met us and gave us the tour of the city once buried in ashes.  What a great experience!  Our guide was so enthused to share his knowledge that we felt as if we were living in Pompeii at its height.  Afterwards, we had lunch at a wine farm on Mt. Vesuvius.  Lovely family run vineyard.  The whole day was outstanding.  For the second and third day, we decided to see the coast by sea and land.  Both were different and both were gorgeous.  Visited Capri and swam in golf of Naples first by sea then drove to different towns along the coast including Positano, Amalfi, and Revello on the second.  It was a nice relaxing break.   

Our final destination was Rome.  We had an general overview tour of the city on the first day.  It was good in a sense it gave us time to get our baring straight.  The second day we met our guide for the tour of the Vatican.  You can visit the Vatican a dozens of times and still not have enough time to see all it has to offer.  In the evening, we had the Colosseum tour.  Definitely one of the highlights.  The last day we had all to ourselves.  We ended up walking around to visit the Spanish steps the Trevi fountain and many more.  We wanted to take in as much as possible.  Even though the trip was 2 weeks, it was too short.  By the end of the trip, our whole family fell in love with this county and we all looked at each other and said can we live here.

Overall, it was an outstanding trip that we can not even begin to describe.   Without the help of our agency, I don't think it would've been possible.  They made sure that every little details were taking care of.  For anyone, who's interested in Italy, please look up this company.  

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Travel Review: Italy Trip, Rome, Sorrento, Florence, Naples, Pompeii, Herculaneum, Ravello, Siena, San Gimignano, Farm & Food Tour

We experienced a fabulous twelve night first trip ever to Europe staying in Rome, Sorrento, and Florence with day visits to Naples, Pompeii and Herculaneum, a drive with stops and photo-ops through the beautiful Amalfi coast villages to Ravello, and a day trip to historic Siena and San Gimignano through the Chianti region of Tuscany. Our travel consultant and her colleague at the company in Rome, proved to be perceptive to our interests, resourceful in finding spot-on solutions within our budget and patient professionals as we explored various itinerary options. Both women spoke and wrote english very well to thoughtfully help us plan our itinerary for three adults with private transportation and guides. Our private guides in Rome; in Pompeii and Herculaneum; in Naples; one a Canadian ex-pat in Florence; and in Siena, informed our discovery of each locale and its many treasures.  We also did two small group tours. First, a farm/food tour near Sorrento with an incredibly informative and entertaining guide, and catacombs at Saint Sebastian with a nameless guide and small group of 9 during our Appian way visit and final full day in Rome. At times we were chaperoned in private vehicles with english speaking drivers knowledgeable of their territories. In Rome, in Naples, in the Bay of Naples Sorrento area, in Tuscany, and in Amalfi. We wouldn't hesitate to recommend this company to help others plan the vacation of a lifetime.

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